Conor and Tiffany first met at Lincoln High School during her first year and his second year of teaching. Despite being colleagues, they hadn't run into each other in the hallway. They first formally met at after school drinks at Stillwater Tavern in Smithfield (RIP). After weeks of casually nodding during passing time or meetings, Tiffany finally had the courage to walk up to Conor during Spirit Week on "Skit Night" and the rest is history.

Conor finally asked for Tiffany's phone number at Parente's Restaurant. The following week, Tiffany texted Conor and "cancelled" their first date. Conor, being a social butterfly, quickly made dinner plans with his brother, Dan, his best friend and best man, for that evening. At after school drinks, once again at Stillwater Tavern (RIP), Tiffany showed up and "forgot" that she "cancelled" on Conor only days earlier. So long story short, Conor, Tiffany... and Dan had a beautiful first date at Flatbread Pizza in Providence, then Hope Street Pizza, then Ivy Tavern... Anyway, it worked out.

Tiffany and Conor planned a weekend get away to one of their favorite places, Bar Harbor, Maine. Conor's plan was to ask Tiffany on her favorite hike, the Precipice Trail in Acadia National Park. That morning, however, Mother Nature had other plans and it rained for hours. Consequently, Conor and Tiffany walked to Otter Cliff to avoid the slippery conditions of the Precipice, where Conor eventually got down on one knee. Even though Conor forgot how to speak english in that moment, Tiffany still knew to say yes. As they walked back to begin celebrating, Bill, Cindy, Dick, Betsy, Haley, and Dan were among the first phone calls to share the news.